# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1970776'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3098(15)
_cell_length_b                   10.3197(17)
_cell_length_c                   18.503(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.529(2)
_cell_angle_gamma                90
_cell_volume                     1777.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3482
_cell_measurement_theta_min      0.233
_cell_measurement_theta_max      25.993

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'LIGHT YELLOW'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10634
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3482
_reflns_number_gt                1464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3482
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1567
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_restrained_S_all      0.864
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5971(2) 0.46609(17) 0.08960(8) 0.0558(5) Uani 1 1 d . . . . .
O2 O 0.3999(2) 0.19281(19) 0.29475(9) 0.0736(6) Uani 1 1 d . . . . .
N1 N 0.3605(2) 0.43633(19) 0.05025(10) 0.0523(6) Uani 1 1 d . . . . .
H1 H 0.3694 0.4608 0.0062 0.063 Uiso 1 1 calc R U . . .
N2 N 0.6322(2) 0.4004(2) 0.23318(10) 0.0551(6) Uani 1 1 d . . . . .
H2 H 0.6642 0.4414 0.1965 0.066 Uiso 1 1 calc R U . . .
C1 C 0.2324(3) 0.3937(2) 0.07954(13) 0.0484(7) Uani 1 1 d . . . . .
C2 C 0.2571(3) 0.3641(2) 0.15287(13) 0.0472(7) Uani 1 1 d . . . . .
C3 C 0.1408(3) 0.3242(3) 0.19282(15) 0.0616(8) Uani 1 1 d . . . . .
H3 H 0.1524 0.3057 0.2418 0.074 Uiso 1 1 calc R U . . .
C4 C 0.0072(3) 0.3124(3) 0.15856(16) 0.0710(9) Uani 1 1 d . . . . .
H4 H -0.0706 0.2852 0.1852 0.085 Uiso 1 1 calc R U . . .
C5 C -0.0137(3) 0.3398(3) 0.08600(17) 0.0701(9) Uani 1 1 d . . . . .
H5 H -0.1045 0.3300 0.0645 0.084 Uiso 1 1 calc R U . . .
C6 C 0.0994(3) 0.3815(3) 0.04525(14) 0.0589(8) Uani 1 1 d . . . . .
H6 H 0.0866 0.4007 -0.0036 0.071 Uiso 1 1 calc R U . . .
C7 C 0.4099(3) 0.3874(2) 0.16802(12) 0.0459(7) Uani 1 1 d . . . . .
C8 C 0.4701(3) 0.4341(2) 0.10079(13) 0.0473(7) Uani 1 1 d . . . . .
C9 C 0.4927(3) 0.3676(2) 0.22922(12) 0.0461(7) Uani 1 1 d . . . . .
C10 C 0.4276(3) 0.3078(3) 0.29562(13) 0.0499(7) Uani 1 1 d . . . . .
C11 C 0.3940(3) 0.3935(2) 0.35682(12) 0.0466(7) Uani 1 1 d . . . . .
C12 C 0.4066(3) 0.5266(3) 0.35155(13) 0.0578(8) Uani 1 1 d . . . . .
H12 H 0.4412 0.5638 0.3097 0.069 Uiso 1 1 calc R U . . .
C13 C 0.3676(3) 0.6043(3) 0.40855(16) 0.0731(9) Uani 1 1 d . . . . .
H13 H 0.3735 0.6939 0.4046 0.088 Uiso 1 1 calc R U . . .
C14 C 0.3201(3) 0.5492(3) 0.47112(16) 0.0774(10) Uani 1 1 d . . . . .
H14 H 0.2954 0.6016 0.5097 0.093 Uiso 1 1 calc R U . . .
C15 C 0.3090(3) 0.4167(4) 0.47680(14) 0.0730(9) Uani 1 1 d . . . . .
H15 H 0.2768 0.3799 0.5193 0.088 Uiso 1 1 calc R U . . .
C16 C 0.3451(3) 0.3385(3) 0.42017(13) 0.0596(8) Uani 1 1 d . . . . .
H16 H 0.3369 0.2490 0.4241 0.072 Uiso 1 1 calc R U . . .
C17 C 0.7342(3) 0.3758(3) 0.29060(12) 0.0502(7) Uani 1 1 d . . . . .
C18 C 0.8239(3) 0.4740(3) 0.31188(14) 0.0646(8) Uani 1 1 d . . . . .
H18 H 0.8141 0.5557 0.2911 0.078 Uiso 1 1 calc R U . . .
C19 C 0.9291(3) 0.4518(3) 0.36428(16) 0.0779(10) Uani 1 1 d . . . . .
H19 H 0.9903 0.5187 0.3788 0.093 Uiso 1 1 calc R U . . .
C20 C 0.9437(3) 0.3326(3) 0.39476(16) 0.0808(10) Uani 1 1 d . . . . .
H20 H 1.0149 0.3180 0.4300 0.097 Uiso 1 1 calc R U . . .
C21 C 0.8546(4) 0.2348(3) 0.37375(17) 0.0849(11) Uani 1 1 d . . . . .
H21 H 0.8641 0.1536 0.3952 0.102 Uiso 1 1 calc R U . . .
C22 C 0.7496(3) 0.2551(3) 0.32067(15) 0.0696(9) Uani 1 1 d . . . . .
H22 H 0.6901 0.1875 0.3055 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.250(3) . ?
O2 C10 1.215(3) . ?
N1 C8 1.365(3) . ?
N1 C1 1.394(3) . ?
N2 C9 1.342(3) . ?
N2 C17 1.429(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.390(4) . ?
C2 C7 1.462(3) . ?
C3 C4 1.386(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.380(4) . ?
C7 C9 1.368(3) . ?
C7 C8 1.460(3) . ?
C9 C10 1.515(3) . ?
C10 C11 1.477(3) . ?
C11 C12 1.382(3) . ?
C11 C16 1.390(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.373(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.371(4) . ?
C17 C18 1.365(3) . ?
C17 C22 1.370(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.358(4) . ?
C20 C21 1.357(4) . ?
C21 C22 1.383(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 111.1(2) . . ?
C9 N2 C17 128.2(2) . . ?
C6 C1 N1 128.0(2) . . ?
C6 C1 C2 123.1(3) . . ?
N1 C1 C2 108.9(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 C7 135.6(2) . . ?
C1 C2 C7 106.4(2) . . ?
C4 C3 C2 119.0(3) . . ?
C5 C4 C3 121.9(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 117.7(3) . . ?
C9 C7 C8 122.3(2) . . ?
C9 C7 C2 131.1(2) . . ?
C8 C7 C2 106.5(2) . . ?
O1 C8 N1 125.1(2) . . ?
O1 C8 C7 127.9(2) . . ?
N1 C8 C7 107.0(2) . . ?
N2 C9 C7 122.0(2) . . ?
N2 C9 C10 117.7(2) . . ?
C7 C9 C10 120.2(2) . . ?
O2 C10 C11 123.1(2) . . ?
O2 C10 C9 118.4(2) . . ?
C11 C10 C9 118.4(2) . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 C10 121.4(2) . . ?
C16 C11 C10 118.9(2) . . ?
C13 C12 C11 119.9(3) . . ?
C14 C13 C12 120.0(3) . . ?
C13 C14 C15 120.2(3) . . ?
C16 C15 C14 120.4(3) . . ?
C15 C16 C11 119.8(3) . . ?
C18 C17 C22 120.1(3) . . ?
C18 C17 N2 118.2(2) . . ?
C22 C17 N2 121.6(2) . . ?
C17 C18 C19 119.8(3) . . ?
C20 C19 C18 120.3(3) . . ?
C21 C20 C19 120.0(3) . . ?
C20 C21 C22 120.4(3) . . ?
C17 C22 C21 119.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C6 -179.5(2) . . . . ?
C8 N1 C1 C2 1.1(3) . . . . ?
C6 C1 C2 C3 -1.9(4) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
C6 C1 C2 C7 179.1(2) . . . . ?
N1 C1 C2 C7 -1.4(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C7 C2 C3 C4 -179.7(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
N1 C1 C6 C5 -178.5(2) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C3 C2 C7 C9 5.3(5) . . . . ?
C1 C2 C7 C9 -175.9(3) . . . . ?
C3 C2 C7 C8 -177.6(3) . . . . ?
C1 C2 C7 C8 1.2(3) . . . . ?
C1 N1 C8 O1 179.4(2) . . . . ?
C1 N1 C8 C7 -0.2(3) . . . . ?
C9 C7 C8 O1 -2.7(4) . . . . ?
C2 C7 C8 O1 179.8(2) . . . . ?
C9 C7 C8 N1 176.8(2) . . . . ?
C2 C7 C8 N1 -0.6(3) . . . . ?
C17 N2 C9 C7 -174.2(2) . . . . ?
C17 N2 C9 C10 6.3(4) . . . . ?
C8 C7 C9 N2 5.9(4) . . . . ?
C2 C7 C9 N2 -177.4(2) . . . . ?
C8 C7 C9 C10 -174.6(2) . . . . ?
C2 C7 C9 C10 2.2(4) . . . . ?
N2 C9 C10 O2 -107.2(3) . . . . ?
C7 C9 C10 O2 73.2(3) . . . . ?
N2 C9 C10 C11 75.9(3) . . . . ?
C7 C9 C10 C11 -103.7(3) . . . . ?
O2 C10 C11 C12 -169.9(3) . . . . ?
C9 C10 C11 C12 6.8(4) . . . . ?
O2 C10 C11 C16 8.3(4) . . . . ?
C9 C10 C11 C16 -174.9(2) . . . . ?
C16 C11 C12 C13 -1.4(4) . . . . ?
C10 C11 C12 C13 176.8(2) . . . . ?
C11 C12 C13 C14 1.8(4) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C11 0.4(4) . . . . ?
C12 C11 C16 C15 0.3(4) . . . . ?
C10 C11 C16 C15 -177.9(3) . . . . ?
C9 N2 C17 C18 -135.6(3) . . . . ?
C9 N2 C17 C22 48.8(4) . . . . ?
C22 C17 C18 C19 -0.7(4) . . . . ?
N2 C17 C18 C19 -176.3(2) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C18 C17 C22 C21 1.4(4) . . . . ?
N2 C17 C22 C21 176.9(3) . . . . ?
C20 C21 C22 C17 -1.5(5) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041

